SU562553A1 - Method for preparing 0-benzoyl derivatives of 3-hydroxy (2-hydroxy) -1,2,3,4-tetrahydroquinolines - Google Patents

Description

one

This invention relates to a process for the preparation of O-benzoshshnyh derivatives of 3-hydroxy- (2-6xy) -1,2,3,4-tvtrapndro sholnnov, direct mvn kyo xs for sstea derivatives of 1,2,3,4-tvtragadroquinolyush and benoquinolite can be used as intermediate products for the study of dyed products, as well as in other areas: the production industry.

The known method of i-luchev and O-hydroxy derivatives of a 3-hydroxy-1,2,3,4-tetraprobrobenzo L 1 1 hgayupina derivative by producing 3-hydroxy-1, 2,3,4-g € trahydrobenzo C b quinoline with an equimolecular amount of benzoyl chloride in the medium pyridine l. However, the yield of the target product is not specified. Upon kupyukokratny repetition of this reaction, 1B (and it turned out that when acylated by the above method, a mixture of

K1, O-monoash compounds, N, O-iash derivatives, and only a small amount of the starting material remains - H-Yux-1 | , 2,3,4-tetrahydrrbenzo 1 and quinoline I. The output of the O-acic derivative of 3-hydroxy-1, 2,3,4-tetragvdrobenzo | 13 quinopine

is 25-30%. With an increase in the amount of the expanding agent in the reacaiine mixture, the original substance does not remain, in addition, the amount of the / H-, 0-ibenzoyl derivative increases, the amount of oxygen does not increase, the yield of the latter even decreases,

The purpose of the invention is to increase the yield of the target product.

This is achieved by the fact that N-bioisoyl derivatives of 3-hydroxy (2-hydroxy) -1,2,3,4-tetragndrohnnolines are treated with dimbutyl sulfonic acid, phosphorus CHLORIDE WITH TIONHSH1 chloride.

The described method of producing O-6ei derivatives of 3-hydroxy () -1, 2,3,4-tetrahydroquinolines is concluded that li-benzoyl 3-hydroxy (2-hydroxy) -1,2,3,4-tetrahydroquinopine derivatives treated with dimetipsulfoxide, phosphorus chloroxene or chlorine thionyl, mainly in dichloroethane.

Example 1. Ester of benzoic acid and 3-hydroxy-1,2,3,4-tetrahydrobenzo tl J quinoline (I).

1.5 g (0, ОО5 g. Mol) of N-benzoyl-3-hydroxy-1, 2,. Tetrahydrobenzo-til quinoline, 15 ml of dimethyl sulphate and 1.25 g of potassium bicarbonate are heated for 1-2 hours at 110 C. The mixture is diluted water and extract with ether. The residue, after removal of the ether, is recrystallized from methanol.

Similarly receive: benzoic ester

acids and 3-hydroxy-6-chloro-1,2,3,4-tetrahydrobenzo-LP-quinoline (II), benzoic acid ester and 3-hydroxy-6-methyl-1,2,3,4-tetrahydrobenzo p-quinoline (III), ester of acetic acid and indano fl, 7- j 1,2,3,4-tetrahydro-Z-hydroxyquinoline (IV). benzoic acid and indano {1, 1,2,3,4-tetrahydro-3-hydroxyquinoline (Y) ester, benzoic acid and 2-hydroxy-1,2,3,4-tetragvdrobenzo f quinoline {V1) ester, Analysis data are shown in the table.

I83.3 124.5-125.0 N0 Я71.0 156.0-156.5 16 g 172.0 121.0-122.0 Example 2. Compound 1. 1.3 g (O.OO5 Humol) N-benzoyl-3 -Oxy-1 .2,3,4-tvtragidrobenao L bnnolyn 0.0 g (O, 0075) thion chloride and 35 ml of dichloroethane are mixed at room temperature for 30 times. The mixture is poured onto ice (30 g), basified and extracted with ether. The residue, after removal of the ester, is converted from methanol. Yield 95.3%. Similarly receive: compound V 96.44%, compound VI - 96.0%. Depression of the melting point with compounds G, Y, VI, obtained according to example 1, does not give. 17 i. 3429 () 1721 (CO) in c 10 5 10.5 L0.5 342Y (NH) 1720 (CO) 3409 (UH) 1719 (CO) 3428 CNH) 1720 (CO) 3407 (NH) .7 1722 (CO) Example 3 Compound T 1.5 g (O, OO5) of N-benzoyl-3-hydroxy-1 .2.3,4-tetragndrobenzo111 J quinoline and 1.9 g of O, O125 Gmol) of phosphorus oxychloride are stirred at room temperature for 10 hours. The reaction 4 mixture is poured onto ice (ZO g). The precipitate formed is filtered off, washed with water and shaken with an aqueous solution of sodium carbonate in the presence of ether. Exit 97.3%. Similarly receive: compound II 97%. compound 111 -96.8%. Compound 95 .5%. Compound V —95.7%; Compound VI — 96.6%. Depression of melting temperature; compounds I, II, P1, 1Y, V, VI obtained according to example 1, does not give.

Example 4. Compound I. 1.5 g (0, OO5 gmol) N-benzoyl 3-oxig -1, 2,3,4-chtratirobenzo111 J quinoline, 1.9 g GO, 0125 g, mol) phosphorus oxychloride and 30 ml of dichloroethane are stirred at room temperature for 3 hours. The solution is isolated in the same manner as in Example 3. Yield 96, O%.

Similarly receive: compound II 94, 6%, compound 111-96.2%, compound P - 95.5%, compound 96.9%, compound N1 -9c, 0%.

Claims (2)

1. The method of obtaining the O-benzoyl derivatives of 3-hydroxy-2-yuxi) -1,2,3,4-tetrahydroquinolines, differs in that in order to increase the yield of the target product, N-benzoic derivatives 3- Oxn- (2-hydroxy) -1,2,3,4 "-Getragidroquinolines are treated with cimethylsulfoxindum, phosphorus oxychloride or thionyl chloride. 2. A method according to claim 1, characterized in that the treatment with thionyl chloride is carried out in dichloroethane. Sources of information taken into account in the examination: 1. Vorozhtsov N.N., Kutkevichus S.I. Study of the products of the interaction of epichlorohydrin with apoMaTH4ecKHNffl amines, JOH, 1957, S3. 2521.